Scott Sternberg is the creative force behind the label Band of Outsiders which began after Sternberg left his job as a Hollywood talent agent in 2003 to begin his own consulting business. While working as a brand consultant for Target, he realized he had a "knack" for designing clothing. In an interview with the Wall Street Journal he said, "It wasn't like I felt I had a calling for, you know, fashion. I just wanted to make a great shirt and a great tie for myself. I don't know why, but that was the instinct and I thought I could do it." We can see the results of his impetus to create clothing rather than "fashion" through his well documented success.

His first collections were comprised of menswear only. He "deconstructed" preppy schoolboy style to the delight of high end retailers such as Barney's. While his deconstructed look was an homage to indie-cool (think hipsters mocking the status quo by donning the clothing that defines it), his hand-tailored pieces were a hit in big name department stores and the fashion world took notice, awarding him the CFDA award in 2009. Sternberg has since expanded his line with not one, but two womenswear labels. The first, called Boy, is a menswear-inspired line while the second, called Girl, is a diffusion line with stronger feminine accents. For now, both lines are shown under the Band of Outsiders label, rather than their secondary names. In interviews, Sternberg is the epitome of his ideal customer: brash and outspoken with a "nerdy" cool aesthetic vibe. He's also firmly set against entering the world of New York fashion (he lives in L.A.) in order to continue creating clothing that isn't influenced by it.

In spite of his success, some in the fashion world have questioned if he's a one trick pony, capable only of creating a high end J.Crew-esque look that might lose its appeal once the trend is over. Sternberg disagrees. In an interview with Esquire he says, "It doesn't worry me at all. I do what I do, and when I look at clothes dating back to the 1920s, there have always been men who dress in variations on preppy. The proportions change, but that style, that way of dressing, is there." Check out some of Sternberg's recent womenswear looks and decide for yourself if it's possible to make the transition from talent agent to talented designer.

Jennifer Davidson joined theFashionSpot team as Managing Editor in November 2010. In addition to overseeing the editorial content of the site, she shares her fashion, beauty, and pop culture obsessions in her weekly column The Love List. Prior to joining the tFS team, Jennifer produced fashion segments for television, and is also the co-founder of StyleBakery.com.